DE2449340C2 - Verfahren zur Herstellung von Pyridin und 3-Methylpyridin - Google Patents
Verfahren zur Herstellung von Pyridin und 3-MethylpyridinInfo
- Publication number
- DE2449340C2 DE2449340C2 DE2449340A DE2449340A DE2449340C2 DE 2449340 C2 DE2449340 C2 DE 2449340C2 DE 2449340 A DE2449340 A DE 2449340A DE 2449340 A DE2449340 A DE 2449340A DE 2449340 C2 DE2449340 C2 DE 2449340C2
- Authority
- DE
- Germany
- Prior art keywords
- reactor
- acrolein
- catalyst
- methylpyridine
- pyridine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 title claims description 72
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 72
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 100
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 68
- 239000003054 catalyst Substances 0.000 claims description 54
- 239000007789 gas Substances 0.000 claims description 45
- 229910021529 ammonia Inorganic materials 0.000 claims description 34
- 239000011261 inert gas Substances 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- -1 aluminum silicates Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000012495 reaction gas Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- LDDQLRUQCUTJBB-UHFFFAOYSA-O azanium;hydrofluoride Chemical compound [NH4+].F LDDQLRUQCUTJBB-UHFFFAOYSA-O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/08—Preparation by ring-closure
- C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
- C07D213/12—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from unsaturated compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2449340A DE2449340C2 (de) | 1974-10-17 | 1974-10-17 | Verfahren zur Herstellung von Pyridin und 3-Methylpyridin |
| ZA00756242A ZA756242B (en) | 1974-10-17 | 1975-10-01 | A process for producing pyridine and 3-methyl-pyridine |
| US05/622,488 US4171445A (en) | 1974-10-17 | 1975-10-15 | Process for the production of pyridine and 3-methyl pyridine |
| GB42207/75A GB1512650A (en) | 1974-10-17 | 1975-10-15 | Production of pyridine and 3-methyl pyridine |
| IT51782/75A IT1047772B (it) | 1974-10-17 | 1975-10-15 | Procedimento per la produzione di piridina e 3 metilpiridina |
| BR7506760*A BR7506760A (pt) | 1974-10-17 | 1975-10-15 | Processo para a fabricacao de piridina e 3-metil-piridina |
| CH1347175A CH599156A5 (cs) | 1974-10-17 | 1975-10-16 | |
| CA237,881A CA1037046A (en) | 1974-10-17 | 1975-10-17 | Process for producing pyridine and 3-methyl pyridine |
| BE6045222A BE834648A (fr) | 1974-10-17 | 1975-10-17 | Procede pour la fabrication de pyridine et de 3-methylpyridine et produits obtenus |
| FR7531929A FR2288088A1 (fr) | 1974-10-17 | 1975-10-17 | Procede de fabrication de pyridine et de 3-methylpyridine |
| JP50125238A JPS5165767A (en) | 1974-10-17 | 1975-10-17 | Pirijinoyobi 33 mechirupirijinnoseiho |
| NLAANVRAGE7512224,A NL185718C (nl) | 1974-10-17 | 1975-10-17 | Werkwijze voor het bereiden van pyridine en 3-methylpyridine door katalytische omzetting van acroleine met ammoniak in de gasfase. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2449340A DE2449340C2 (de) | 1974-10-17 | 1974-10-17 | Verfahren zur Herstellung von Pyridin und 3-Methylpyridin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2449340A1 DE2449340A1 (de) | 1976-04-22 |
| DE2449340C2 true DE2449340C2 (de) | 1987-04-09 |
Family
ID=5928464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2449340A Expired DE2449340C2 (de) | 1974-10-17 | 1974-10-17 | Verfahren zur Herstellung von Pyridin und 3-Methylpyridin |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4171445A (cs) |
| JP (1) | JPS5165767A (cs) |
| BE (1) | BE834648A (cs) |
| BR (1) | BR7506760A (cs) |
| CA (1) | CA1037046A (cs) |
| CH (1) | CH599156A5 (cs) |
| DE (1) | DE2449340C2 (cs) |
| FR (1) | FR2288088A1 (cs) |
| GB (1) | GB1512650A (cs) |
| IT (1) | IT1047772B (cs) |
| NL (1) | NL185718C (cs) |
| ZA (1) | ZA756242B (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2554946A1 (de) * | 1975-12-06 | 1977-06-23 | Degussa | Verfahren zur gewinnung von pyridin und 3-methylpyridin |
| DE2639702C2 (de) * | 1976-09-03 | 1984-03-08 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von 2,3-Cycloalkenopyridinen |
| DE2703049C2 (de) * | 1977-01-26 | 1987-04-16 | Degussa Ag, 6000 Frankfurt | Verfahren zur Herstellung von Pyridin und 3-Methylpyridin |
| DE2703069A1 (de) * | 1977-01-26 | 1978-07-27 | Degussa | Verfahren zur herstellung von 2-methylpyridin und 3-methylpyridin |
| DE2703070A1 (de) * | 1977-01-26 | 1978-07-27 | Degussa | Verfahren zur herstellung von 3-methylpyridin |
| DE2712694A1 (de) * | 1977-03-23 | 1978-09-28 | Degussa | Verfahren zur herstellung substituierter pyridine |
| DE3741159A1 (de) * | 1987-12-04 | 1989-06-15 | Basf Ag | Verfahren zur herstellung von cyano-pyridinen |
| DE3741160A1 (de) * | 1987-12-04 | 1989-06-15 | Basf Ag | Verfahren zur herstellung von substituierten pyridinen |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1193341A (en) * | 1967-05-11 | 1970-05-28 | Ici Ltd | Catalytic process for the manufacture of Pyridine or Methylpyridines |
| GB1222971A (en) * | 1967-10-06 | 1971-02-17 | Ici Ltd | Catalytic process for the manufacture of pyridine or methylpyridines |
| BE790121A (fr) * | 1971-10-15 | 1973-02-01 | Degussa | Catalyseurs pour la preparation de pyridine et de 3-methylpyridine |
| DE2203384C3 (de) * | 1972-01-25 | 1974-08-22 | Ruetgerswerke Ag, 6000 Frankfurt | Kontinuierliches Verfahren zur Herstellung von Pyridin und beta-Picolin |
| DE2224160C3 (de) * | 1972-05-18 | 1979-10-04 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von Katalysatoren für die Herstellung von Pyridin und 3-Methylpyridin |
| DE2239801C3 (de) * | 1972-08-12 | 1979-08-23 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Verfahren zur Herstellung von Katalysatoren |
-
1974
- 1974-10-17 DE DE2449340A patent/DE2449340C2/de not_active Expired
-
1975
- 1975-10-01 ZA ZA00756242A patent/ZA756242B/xx unknown
- 1975-10-15 US US05/622,488 patent/US4171445A/en not_active Expired - Lifetime
- 1975-10-15 IT IT51782/75A patent/IT1047772B/it active
- 1975-10-15 BR BR7506760*A patent/BR7506760A/pt unknown
- 1975-10-15 GB GB42207/75A patent/GB1512650A/en not_active Expired
- 1975-10-16 CH CH1347175A patent/CH599156A5/xx not_active IP Right Cessation
- 1975-10-17 CA CA237,881A patent/CA1037046A/en not_active Expired
- 1975-10-17 FR FR7531929A patent/FR2288088A1/fr active Granted
- 1975-10-17 BE BE6045222A patent/BE834648A/xx not_active IP Right Cessation
- 1975-10-17 JP JP50125238A patent/JPS5165767A/ja active Pending
- 1975-10-17 NL NLAANVRAGE7512224,A patent/NL185718C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1512650A (en) | 1978-06-01 |
| IT1047772B (it) | 1980-10-20 |
| NL185718B (nl) | 1990-02-01 |
| BR7506760A (pt) | 1976-08-17 |
| BE834648A (fr) | 1976-04-20 |
| DE2449340A1 (de) | 1976-04-22 |
| CH599156A5 (cs) | 1978-05-12 |
| JPS5165767A (en) | 1976-06-07 |
| FR2288088B1 (cs) | 1979-02-02 |
| ZA756242B (en) | 1976-09-29 |
| US4171445A (en) | 1979-10-16 |
| CA1037046A (en) | 1978-08-22 |
| NL7512224A (nl) | 1976-04-21 |
| NL185718C (nl) | 1990-07-02 |
| FR2288088A1 (fr) | 1976-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |